O-Phenylhydroxylamine → HCID 75151422, compound

HRID 2367070Notes

Reaction equation

HRID 2367070 reaction equation
[C:1]1([O:7][NH2:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:9][C:10]1[N:14]([CH2:15][C:16]([N:18]2[CH2:23][CH2:22][CH:21]([C:24]3[S:25][CH:26]=[C:27]([CH:29]=O)[N:28]=3)[CH2:20][CH2:19]2)=[O:17])[N:13]=[C:12]([C:31]([F:34])([F:33])[F:32])[CH:11]=1>C(O)C>[C:1]1([O:7][N:8]=[CH:29][C:27]2[N:28]=[C:24]([CH:21]3[CH2:20][CH2:19][N:18]([C:16](=[O:17])[CH2:15][N:14]4[C:10]([CH3:9])=[CH:11][C:12]([C:31]([F:32])([F:34])[F:33])=[N:13]4)[CH2:23][CH2:22]3)[S:25][CH:26]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 2794249O-PhenylhydroxylamineHCID 86631244HCID 86631244, compound

Product 1

HCID 75151422HCID 75151422, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

At room temperature, O-phenylhydroxylamine (41 mg) and Amberlyst A21 (200 mg) are added to a solution of 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde (100 mg) in ethanol. The reaction mixture is stirred at room temperature for 24 hours. The solvent is then removed under reduced pressure. The residue is purified by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient). This gives 2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-1,3-thiazole-4-carbaldehyde O-phenyl oxime (50 mg, 40%) which consists of an about 9:1 mixture of cis and trans isomers (log P(pH2.7)=3.74 (93%), 3.94 (7%)).

Workup

  1. customThe solvent is then removed under reduced pressure
  2. customThe residue is purified by column chromatography (silica gel, ethyl acetate:hexane 0%-100% elution gradient)
  3. additionabout 9:1 mixture of cis and trans isomers (log P(pH2.7)=3.74 (93%), 3.94 (7%))

Sources & evidence

ORD record
ord-24c4ccf1cf93479a8156a0dae26b4f6c
Source dataset
uspto-grants-2014_04
Patent number
US08697878B2

Reaction notes

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